Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
- Date Wed 24th September 2025 - Wed 22nd October 2025
- Time 5:30PM EDT
- Location Cheshire, Connecticut
- Price Free - $38.10
- Races 8 races
- Distances 5km
Event summary
Join us for the exciting Cheshire Community YMCA Harvest Trail Race and Y Cup Relay, taking place from September 24 to October 22, 2025, in the picturesque Naugatuck Valley at historic Ives Farm! This vibrant event is perfect for participants of all ages, featuring a scenic 5K run that meanders through beautiful fields and trails. The race kicks off at 10:00 AM, right after the FREE Pumpkin Dash for kids aged 6 and younger at 9:45 AM, ensuring a fun-filled day for the whole family.
In addition to the thrilling races, attendees can enjoy a variety of family-friendly activities including pumpkin decorating, face painting, Halloween mask making, games, live music, and a festive fall-themed photo booth. All proceeds from this community-focused event will support the vital work of the YMCA in Cheshire and the revitalization efforts of the Cheshire Land Trust at Ives Farm. Don’t miss your chance to be part of this uplifting and engaging community celebration!
In addition to the thrilling races, attendees can enjoy a variety of family-friendly activities including pumpkin decorating, face painting, Halloween mask making, games, live music, and a festive fall-themed photo booth. All proceeds from this community-focused event will support the vital work of the YMCA in Cheshire and the revitalization efforts of the Cheshire Land Trust at Ives Farm. Don’t miss your chance to be part of this uplifting and engaging community celebration!
Organiser's Description
The Cheshire Community YMCA and Cheshire Land Trust are partnering on a race around historic Ives Farm. This all-ages run will wind through the fields and trails on the property, with the start and finish line located at the beautifully restored barn. Proceeds from this event will support the work that the YMCA does in the Cheshire community as well as the revitalization plans that the Cheshire Land Trust has for the Ives Farm property.
* Prior to the race there will be a FREE Pumpkin Dash for kids 6 years old and younger.
* Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM
* Prior to the race there will be a FREE Pumpkin Dash for kids 6 years old and younger.
* Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM
Races
-
5K Trail Race
Incl. $3.10 Fee & Custom Harvest Trail Race Hat
Sat 25th October 2025 (10:00AM EDT)
$38.10
This trail 5k is a great beginner friendly race with varied terrain and some slight elevation - perfect for the road runner wanting to try a trail run. It's also a good opportunity for an experienced trail runner to do some speed work. -
Y Cup Relay
Incl. $1.90 Fee & Custom Harvest Trail Race Hat
Sat 25th October 2025 (10:05AM EDT)
$16.90
Teams of 3 elementary school students will each run one mile of the 5K course. Teams from all grades will compete for their team to determine which school wins the prestigious Y Cup for the 25-26 school year. This years Y Cup Relay will be run in honor of Coach Jerry Webb who was a beloved Physical Education teacher at Highland School and an active part of the Y Cup Relay since it began. His support and enthusiasm for this event was contagious and resulted in a great turn out of young runners. -
Pumpkin Dash
Incl. Finisher Medal
Sat 25th October 2025 (9:45AM EDT)
Free
A free race for kids 6 and under on the dirt roads of Ives Farm. Kids will get a chance to run through the same race finish line as all other racers. -
Y Cup 5-Week Practice Series - 9/24/2025
Wed 24th September 2025 (5:30PM EDT)
Free
Join us for a special 5-week practice series designed for our young athletes participating in the Y-Cup! This program meets Wednesdays from 5:30-6:30 Sept. 24-Oct 22 at our new YMCA location (435 North Brooksvale Rd. Cheshire). Each practice will focus on building endurance, improving speed, and developing proper running mechanics. Our goal is to help participants gain confidence, strengthen their performance, and prepare for race day on the Harvest Trail. Contact Brandon Riollano at [email protected] or 203-272-3150x511 with questions. -
Y Cup 5-Week Practice Series - 10/01/2025
Wed 1st October 2025 (5:30PM EDT)
Free
Join us for a special 5-week practice series designed for our young athletes participating in the Y-Cup! This program meets Wednesdays from 5:30-6:30 Sept. 24-Oct 22 at our new YMCA location (435 North Brooksvale Rd. Cheshire). Each practice will focus on building endurance, improving speed, and developing proper running mechanics. Our goal is to help participants gain confidence, strengthen their performance, and prepare for race day on the Harvest Trail. Contact Brandon Riollano at [email protected] or 203-272-3150x511 with questions. -
Y Cup 5-Week Practice Series - 10/08/2025
Wed 8th October 2025 (5:30PM EDT)
Free
Join us for a special 5-week practice series designed for our young athletes participating in the Y-Cup! This program meets Wednesdays from 5:30-6:30 Sept. 24-Oct 22 at our new YMCA location (435 North Brooksvale Rd. Cheshire). Each practice will focus on building endurance, improving speed, and developing proper running mechanics. Our goal is to help participants gain confidence, strengthen their performance, and prepare for race day on the Harvest Trail. Contact Brandon Riollano at [email protected] or 203-272-3150x511 with questions. -
Y Cup 5-Week Practice Series - 10/15/2025
Wed 15th October 2025 (5:30PM EDT)
Free
Join us for a special 5-week practice series designed for our young athletes participating in the Y-Cup! This program meets Wednesdays from 5:30-6:30 Sept. 24-Oct 22 at our new YMCA location (435 North Brooksvale Rd. Cheshire). Each practice will focus on building endurance, improving speed, and developing proper running mechanics. Our goal is to help participants gain confidence, strengthen their performance, and prepare for race day on the Harvest Trail. Contact Brandon Riollano at [email protected] or 203-272-3150x511 with questions. -
Y Cup 5-Week Practice Series - 10/22/2025
Wed 22nd October 2025 (5:30PM EDT)
Free
Join us for a special 5-week practice series designed for our young athletes participating in the Y-Cup! This program meets Wednesdays from 5:30-6:30 Sept. 24-Oct 22 at our new YMCA location (435 North Brooksvale Rd. Cheshire). Each practice will focus on building endurance, improving speed, and developing proper running mechanics. Our goal is to help participants gain confidence, strengthen their performance, and prepare for race day on the Harvest Trail. Contact Brandon Riollano at [email protected] or 203-272-3150x511 with questions.
Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
